1,4-dihydropyridine
   HOME

TheInfoList



Click Here for Items Related To - 1,4-dihydropyridine
OR:
1,4-dihydropyridine on:   [Wikipedia]   [Google]   [Amazon]

1,4-Dihydropyridine (DHP) is an
organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...
with the formula CH2(CH=CH)2NH. The parent compound is uncommon, but derivatives of 1,4-dihydropyridine are important commercially and biologically. The pervasive cofactors
NADH Nicotinamide adenine dinucleotide (NAD) is a coenzyme central to metabolism. Found in all living cells, NAD is called a dinucleotide because it consists of two nucleotides joined through their phosphate groups. One nucleotide contains an ade ...
and
NADPH Nicotinamide adenine dinucleotide phosphate, abbreviated NADP or, in older notation, TPN (triphosphopyridine nucleotide), is a cofactor used in anabolic reactions, such as the Calvin cycle and lipid and nucleic acid syntheses, which require N ...
are derivatives of 1,4-dihydropyridine. Dihydropyridine calcium channel blockers are a class of L-type calcium channel blockers used in the treatment of hypertension. 1,2-Dihydropyridines are also known.


Properties and reactions

A recurring feature of 1,4-dihydropyridines is the presence of substituents at the 2- and 6-positions. Dihydropyridines are
enamine An enamine is an unsaturated compound derived by the condensation of an aldehyde or ketone with a secondary amine. Enamines are versatile intermediates. The word "enamine" is derived from the affix ''en''-, used as the suffix of alkene, and the r ...
s, which otherwise tend to tautomerize or hydrolyze. The dominant reaction of dihydropyridines is their ease of oxidation. In the case of dihydropyridines with hydrogen as the substituent on nitrogen, oxidation yields
pyridine Pyridine is a basic (chemistry), basic heterocyclic compound, heterocyclic organic compound with the chemical formula . It is structurally related to benzene, with one methine group replaced by a nitrogen atom . It is a highly flammable, weak ...
s: :CH2(CH=CR)2NH → C5H3R2N + H2 The naturally-occurring dihydropyridines NADH and NADPH contain N-alkyl groups. Therefore, their oxidation does not yield pyridine, but N-alkylpyridinium cations: :CH2(CH=CR)2NR' → C5H3R2NR' + H−


Hantzsch ester

Hantzsch ester


See also

* Dihydropyridine receptor * Ryanodine receptor


References


External links

* {{MeshName, Dihydropyridines